There are two online technology essay writers who I truly enjoy reading: Scott Berkun and Paul Graham. Paul is probably the more well known of the two given his Hacker and Painters book, but I think that both have a unique insights in the software industry and the development process. Both are excellent writers who take a deeper, philosophical look at human nature and the specifically the traits of professionals, they investigate the fundamentals of human collaboration, and the ways that it impacts our daily lifes Paul's background is in Lisp programming, while Scott's is in program management and UI design. If you want to sample Paul Graham I suggest you start with "Made in the USA", for Scott Berkun I suggest his recent "Why Smart People Defend Bad Ideas".
What triggered this posting is that Scott Berkun now also has a book out: "The Art of Project Management" which I think is very much worthwhile reading for anyone involved in project management. There is a lot of useful food for thought in this book as well as many pratical suggestions, and this week it will land on the desks of the people that work for and with me as "suggested reading". A sample chapter can be found at Scott's book site, if you are interested in sampling before you buy.